Hydrochloric Acid → HCID 23139028, compound

HRID 1171750Notes

Reaction equation

HRID 1171750 reaction equation
C([S:4][CH:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])[CH2:7]/[C:6]/1=[CH:24]\[C:25]1[CH:29]=[N:28][N:27]([CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[N:26]=1)(=O)C.[ClH:38].C(=O)([O-])O.[Na+]>C(O)C>[ClH:38].[CH:14]1([C:12](=[O:13])[CH:11]([N:8]2[CH2:9][CH2:10][CH:5]([SH:4])/[C:6](=[CH:24]/[C:25]3[CH:29]=[N:28][N:27]([CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[N:26]=3)/[CH2:7]2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23139092HCID 23139092, compound

Product 1

HCID 23139028HCID 23139028, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (E)-4-(acetylsulfanyl)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-({2-[3-(ethoxycarbonyl)propyl]-2H-1,2,3-triazol-4-yl}methylidene)piperidine (570 mg) in ethanol (50 ml) was introduced HCl gas at 0° C. for 30 minutes. The mixture was stirred under tightly sealed condition for 2 hours, and the solvent and excess hydrogen chloride were removed in vacuo. The residue was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: acetonitrile/0.024 N HCl, 35/65, v/v) to afford a fraction containing the product. This fraction was treated with a saturated aqueous sodium hydrogen carbonate solution, and the liberated base was extracted with ethyl acetate to afford the free base of the title compound.

Workup

  1. customthe solvent and excess hydrogen chloride were removed in vacuo
  2. customThe residue was purified by preparative HPLC (YMC-Pack ODS-A
  3. customYMC, eluent: acetonitrile/0.024 N HCl, 35/65, v/v) to afford a fraction
  4. additioncontaining the product
  5. extractionthe liberated base was extracted with ethyl acetate

Sources & evidence

ORD record
ord-ed04da0d3db94f238e910e0f7569d787
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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